Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C20H34O5 |
Molecular Weight | 354.481 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O
InChI
InChIKey=GMVPRGQOIOIIMI-DWKJAMRDSA-N
InChI=1S/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h12-13,15-17,19,21,23H,2-11,14H2,1H3,(H,24,25)/b13-12+/t15-,16+,17+,19+/m0/s1
Molecular Formula | C20H34O5 |
Molecular Weight | 354.481 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 1 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/14725489
Sources: https://www.ncbi.nlm.nih.gov/pubmed/14725489
Ecraprost [AS 013, Circulase] is a prodrug of prostaglandin E(1) within lipid microspheres that is being developed in Japan by Mitsubishi Pharma Corporation and Asahi Glass. It was originally in development with Welfide Corporation. On 1 October 2001, Welfide Corporation (formerly Yoshitomi) merged with Mitsubishi-Tokyo Pharmaceuticals to form Mitsubishi Pharma Corporation. The new company is a subsidiary of Mitsubishi Chemical. Taisho and Seikagaku Corporation had been involved in the development of ecraprost but discontinued their licences to do so. The effects of ecraprost on reperfusion injury, in preclinical studies, had been reported by Taisho. Ecraprost is in phase II in Japan and was in phase II in Europe for the treatment of peripheral arterial disease. It was also in a phase II study in the treatment of diabetic neuropathies. However, this is no longer an active indication. A phase III trial using a lipid emulsion of ecraprost [Circulase] is underway with Mitsubishi Pharma Corporation in the US, using ecraprost for the treatment of patients with severe peripheral arterial disease, which, because of decreased blood flow to the extremities, can lead to painful ulcers on the legs and feet and subsequent amputation. Alpha Therapeutic Corporation (a former subsidiary of Mitsubishi Pharma) was initially involved in trials of ecraprost in the US, but this responsibility has been taken over by the parent company.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1811 Sources: http://www.genome.jp/dbget-bin/www_bget?D02723 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Palliative | PROSTIN VR PEDIATRIC Approved UsePROSTIN VR PEDIATRIC Sterile Solution is indicated for palliative, not definitive, therapy to temporarily maintain the patency of the ductus arteriosus until corrective or palliative surgery can be performed in neonates who have congenital heart defects and who depend upon the patent ductus for survival. Such congenital heart defects include pulmonary atresia, pulmonary stenosis, tricuspid atresia, tetralogy of Fallot, interruption of the aortic arch, coarctation of the aorta, or transposition of the great vessels with or without other defects. Launch Date1981 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
7.09 pg/mL |
20 μg single, intravenous dose: 20 μg route of administration: Intravenous experiment type: SINGLE co-administered: |
ALPROSTADIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
174 pg × min/mL |
20 μg single, intravenous dose: 20 μg route of administration: Intravenous experiment type: SINGLE co-administered: |
ALPROSTADIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
9.5 min |
20 μg single, intravenous dose: 20 μg route of administration: Intravenous experiment type: SINGLE co-administered: |
ALPROSTADIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
7% |
20 μg single, intravenous dose: 20 μg route of administration: Intravenous experiment type: SINGLE co-administered: |
ALPROSTADIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
PubMed
Title | Date | PubMed |
---|---|---|
Effect of lipo-pro-prostaglandin E1, AS-013 on rat inner ear microcirculatory thrombosis. | 1998 Sep |
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Ecraprost: AS 013, Circulase. | 2004 |
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Adjunctive parenteral therapy with lipo-ecraprost, a prostaglandin E1 analog, in patients with critical limb ischemia undergoing distal revascularization does not improve 6-month outcomes. | 2007 May |
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Antiplatelet and anticoagulant drugs for prevention of restenosis/reocclusion following peripheral endovascular treatment. | 2012 Aug 15 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17350216
Patients meeting clinical and hemodynamic criteria for critical limb ischemia who were undergoing either bypass or endovascular revascularization of the below knee popliteal or more distal arteries were randomized to receive placebo or a 60-microg dose of lipo-ecraprost administered intravenously starting Route of Administration:
Intravenous
Substance Class |
Chemical
Created
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Record UNII |
F5TD010360
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Record Status |
Validated (UNII)
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WHO-ATC |
G04BE01
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NDF-RT |
N0000175454
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NDF-RT |
N0000007706
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LOINC |
12837-1
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LOINC |
14005-3
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WHO-VATC |
QC01EA01
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FDA ORPHAN DRUG |
70092
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NDF-RT |
N0000007706
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NDF-RT |
N0000180189
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LOINC |
70092-2
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FDA ORPHAN DRUG |
88795
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WHO-VATC |
QG04BE01
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NDF-RT |
N0000009059
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N0000007706
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N0000009911
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LOINC |
2852-2
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NCI_THESAURUS |
C78568
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FDA ORPHAN DRUG |
95596
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NDF-RT |
N0000000106
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WHO-ATC |
C01EA01
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LOINC |
70093-0
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F5TD010360
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15544
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DTXSID9022578
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138
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CHEMBL495
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1016000
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165559
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m9257
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PRIMARY | Merck Index | ||
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4425
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PROSTAGLANDIN E1
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DB00770
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C28816
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N0000009059
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PRIMARY | Genitourinary Arterial Vasodilation [PE] | ||
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F5TD010360
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1882
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15551
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N0000009911
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PRIMARY | Venous Vasodilation [PE] | ||
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57397
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SUB05372MIG
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5280723
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212-017-2
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D000527
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598
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BINDER->LIGAND |
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SUB_CONCEPT->SUBSTANCE |
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TARGET -> AGONIST | |||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
USP
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SALT/SOLVATE -> PARENT | |||
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TARGET -> AGONIST | |||
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DERIVATIVE -> PARENT |
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
EP
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Related Record | Type | Details | ||
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METABOLITE -> PARENT |
15-keto-PGE1 has only been detected in vitro in homogenized lung preparations; 15-keto metabolites are less pharmacologically active than the parent compound
IN-VITRO
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METABOLITE -> PARENT |
MAJOR
PLASMA
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METABOLITE -> PARENT |
13,14-dihydro-15-ketoprostaglandin E1 is pulmonary metabolite of PGE1 in dogs.
MAJOR
PLASMA
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PRODRUG -> METABOLITE ACTIVE | |||
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METABOLITE -> PARENT |
15-keto metabolites are less pharmacologically active than the parent compound in vitro using isolated animal organs.
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IMPURITY -> PARENT |
test 1
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
test 1
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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